How would you approach this deal?

[Dan Demers]

My friends in Westport, MA were able to rent an incredible waterfront property for about $1500 / month (split between four of them). The property is set up to have 3 units, but the landlord only rents out the bottom floor because she is weary of having too many tenants. From what I hear, the UMass Dartmouth hockey team beat the place up pretty good back in the 70s, and she's kept it one unit ever since.

She is obviously not getting anywhere near what she could out of the property. Install a few appliances, for the 2nd and 3rd floor units, and she could triple her rent (and the first floor rent could be higher as well). I don't know what she is getting for the summer months, but I would hope she would be renting it out weekly for a good amount of money to vacationers.

I'd like to approach her and work out a deal where I could help her manage and rent out the 2nd and 3rd floor units, but where I would agree to be liable for certain damages, to those units to ease her worries.

She also seems like a possible motivated seller since she is letting the property just sit there without much benefit. I assume she's not making much cash flow, because the value is high and taxes and insurance would eat that up.

One possibility I was thinking is lease option out and make some serious cash flow by renovating the upstairs units. I'd even offer to share some of that cash flow with her to be more convincing. 9 month leases to UMass Dartmouth students, and then big vacation rental money during the summer.

Thanks for reading all of that... How would you approach this deal?